


Something New

by FairyNiamh



Category: Teen Wolf (TV)
Genre: Bets & Wagers, Crossdressing, M/M, Not Beta Read
Language: English
Status: Completed
Published: 2017-03-07
Updated: 2017-03-07
Packaged: 2018-09-30 17:38:26
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 919
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10168250
Author URL: https://archiveofourown.org/users/FairyNiamh/pseuds/FairyNiamh
Summary: A bet leads to something more





	

**Author's Note:**

> March 6th is National Dress Day

It had started off as a drunken bet. Well, drunken on his part. He highly doubted any of the pack were actually drunk, despite the wolfsbane laced whiskey that they were downing.

Five shots and $300 later and Stiles had ordered everything he would need to pull off the bet. Luckily the return would be double that amount. Meaning, since he is a college student in debt, he'll do the stupid bet, or die trying. 

Thus, his current predicament. Now, you might be wondering what the bet is, well, to put it simply; it was for him to wear a dress of their choosing. He had managed to talk them out of Little Red Riding Hood. It was overdone to the point of being cliché. So, they, read he, had purchased a Dorothy outfit and had it delivered to Lydia's house. (Because he did not want to give his dad a heart attack) and she had made some alterations to the dress.

Meaning she had removed the 'shirt' that would cover his chest, but left the 'suspenders' to keep the frilly material up. He looked at the get up and sighed. At least they hadn’t demanded that he wear heels, make-up, and a wig. The dress, panties, garter, and stocking were embarrassing enough.

He had decided to put it on at Derek's because the Alpha was supposed to be out of town for the next few days. With a heavy sigh, he went to take a quick shower to help ease the tension in his muscles. Honestly, the shower should be out lawed. He could probably achieve an orgasm just feeling the water beat down on his body. Ah, if only he had the time, but the pack was due to arrive in a half hour.

He reluctantly left the shower and went to don the evil apparel. 

He started with the red sequin thong, then the white garter belt (which made him feel ridiculous, it wasn't like this was his wedding night... not that he would wear this on his wedding night!) He carefully put on the white stockings and secured them in place with the garter belt. He put on the ridiculous petticoat and fluffed it. Then... and then he carefully put on the blue gingham dress made of satin.

As much as he wanted to hate it, he had to admit, at least to himself, that the feel of the fabric against his bare bottom felt arousing. Shit, he needed to think of something, anything else. He didn’t want the pack to be traumatized by him feeling randy.

He sat down on the couch, closed his eyes, and thought about anything, but how he felt. He fell asleep waiting for the pack and their mockery to arrive. So, you can imagine his surprise when he didn't wake up to laughter, but to gentle touches and to soft whimpering.

"You're not supposed to be back yet," Stiles whispered as Derek ran his hands through his hair.

"I got the weekends wrong. I'm not supposed to meet up with the Nanmu pack until next weekend. The Alpha's mate is in labor. A special time for a pack, not one to be shared with outsiders. Lydia was the one to call and correct me on my way there. How did you wind up like this?" the Alpha said as he ran his hand up and down Stiles' leg.

Stiles moaned at the feeling. "A bet against the pack. Though, I have a suspicion that we were set up. Your pack evidentially sees something we don't"

"I've seen it since I met you in the police station. It scared me, you scared me, and that made me so angry. I had thought that Kate was my mate, then she destroyed my life, and there you were. Perfect, rubbing my nose in my mistake..."

"I never meant," he interrupted.

"No, it's not your fault. Would you like another bet?" Derek asked as he nuzzled Stiles' ear.

"I fear any bet taken right now, would be a sucker's bet."

"Very likely, but I bet you a date that my pack set this up on purpose. Erica knows about my weakness for men in skirts, Lydia knows I like you, Scott will do whatever he thinks is best for you..."

"Or whatever Allison thinks is best for me. You know, you don't have to bet me to get me to go on a date with you. All you have to do is ask."

"Will you wear this on our date?"

"I have some dignity left."

"Then, that's a no?"

"Sweetheart, that's a hell no, but I wouldn't be averse to wearing this in a more intimate setting."

"What can be more intimate than this?" Derek asked, confusion coloring his voice.

Stiles leaned up and captured his lips before finally answering, "Similar to this, but set up by one or both of us; or maybe someplace where the pack can't just come in and 'surprise' us. That thought alone is a real boner killer."

"Maybe you can come with me next weekend. The Nanmu pack is only expecting me to be there Friday. I'm free for the rest of the weekend."

"It's a date. Now, let me get up and change."

Derek let him up and get dressed as he made plans for the next weekend. He had plans... plans that will involve a gallon of lube and plenty sports drinks. Stiles will have to be carried home if he has his way.

~Fin~


End file.
